I did it both ways and it wasn't that bad. For refrence, my 80+ oaks were so bad that I invented the leafdozer9000 for moving piles once I blew them waist high. I really don't want to hear how 'bad' anyone else's is if they didn't need to invent a leaf dozer.
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When the pollen strings were falling, I needed to dump both skimmer baskets before and after work for 2 to 3 weeks. That's it. Mildly annoying at worst. The pool may have been a little cloudy for the time if it was a bad pollen year. The 500 carts handled it fine and didn't even need a cleaning after, but i cleaned them anyway so I slept better about it.